Regioselective Synthesis of Isomeric 3-[1-Substituted Pyrazol-3(5)-yl]indoles from β-Ethylthio-β-indolyl-α,β-unsaturated Ketones,Synthesis

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Regioselective Synthesis of Isomeric 3-[1-Substituted Pyrazol-3(5)-yl]indoles from β-Ethylthio-β-indolyl-α,β-unsaturated Ketones
Synthesis ( IF 2.2 ) Pub Date : 2020-03-30 , DOI: 10.1055/s-0040-1707999
Zemin Mei ₁ , Haifeng Yu ₁ , Peiqiu Liao ₂

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An efficient and highly regioselective synthesis of isomeric 3-[1-substituted pyrazol-3(5)-yl]indoles has been developed by the acid-mediated regioselective cyclocondensation reaction of β-ethyltho-β-indolyl-α,β-unsaturated ketones and monosubstituted hydrazines. In the presence of 1 equivalent of AcOH in refluxing EtOH, the cyclocondensation reaction of β-ethyltho-β- indolyl-α,β-unsaturated ketones with monosubstituted hydrazines yielded 3-(1-substituted pyrazol-5-yl)indoles in excellent yields, while 3-(1-substituted pyrazol-3-yl)indoles were obtained in good yields when the cyclocondensation reaction was carried out in refluxing AcOH.

中文翻译：

由β-乙硫基-β-吲哚基-α，β-不饱和酮类区域选择性合成3-异构体[3-取代的吡唑-3（5）-基]吲哚

通过β-乙基tho-β-吲哚基-α，β-不饱和酮的酸介导的区域选择性环缩合反应，开发了一种高效且高度区域选择性的异构3- [1-取代的吡唑-3（5）-基]吲哚化合物。和单取代的肼。在回流的EtOH中存在1当量的AcOH时，β-乙基邻-β-吲哚基-α，β-不饱和酮与单取代肼的环缩合反应以优异的收率得到3-（1-取代的吡唑-5-基）吲哚当在回流的AcOH中进行环缩合反应时，虽然以良好的产率获得了3-（1-取代的吡唑-3-基）吲哚。

更新日期：2020-03-30

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